152120-58-6

Basic information

• Product Name: N,N′-bis(tert-butoxycarbonyl)-N′′-(4-nitrophenyl)guanidine
• Synonyms: N,N′-bis(tert-butoxycarbonyl)-N′′-(4-nitrophenyl)guanidine
• CAS NO: 152120-58-6
• Molecular Weight: 380.401
• Mol File: 152120-58-6.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: N,N′-bis(tert-butoxycarbonyl)-N′′-(4-nitrophenyl)guanidine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N′-bis(tert-butoxycarbonyl)-N′′-(4-nitrophenyl)guanidine(152120-58-6)
• EPA Substance Registry System: N,N′-bis(tert-butoxycarbonyl)-N′′-(4-nitrophenyl)guanidine(152120-58-6)

Safety Data

• Hazardous Substances Data: 152120-58-6(Hazardous Substances Data)

Upstream product

• 100-01-6 4-nitro-aniline 
• 152120-61-1 tert-butyl (1H-pyrazol-1-ylcarbonoimidoyl)carbamate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 145013-05-4 tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanethioyl)carbamate 
• 152120-54-2 N,N'-bis( tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine 

Downstream Products

• 5901-56-4 N-4-nitrophenylguanidine 

Relevant articles and documents

The utilization of ball milling in synthesis of aryl guanidines through guanidinylation and N-Boc-deprotection sequence

Solid state ball milling was used in guanidinylation reactions of aromatic amines with N,N′-Di-Boc-1H-pyrazole-1-carboxamidine reagent. Reaction conditions are advantageous, and in general reactions proceed in significantly shorter reaction times and in higher yields than under the conventional solution conditions. Mechanochemical conditions were also successfully applied to the cleavage of N-Boc protecting group.

Synthesis of guanidines via the I2 mediated desulfurization of N,N′-di-Boc-thiourea

The I2 mediated desulfurization of N,N′-di-Boc-thiourea was developed. Various primary amines, including sterically and electronically deactivated primary amines, were transformed into the corresponding bis-Boc protected guanidines under mild conditions.

A mild and inexpensive procedure for the synthesis of N, N′ -di-boc-protected guanidines

A novel and efficient synthetic procedure for converting a diverse set of amines to N,N′-di-Boc-protected guanidines is described. The methodology comprises the use of cyanuric chloride (TCT) as activating reagent for di-Boc-thiourea. The employ of inexpensive TCT instead of classical HgCl 2 eliminates the environmental hazard of heavy-metal waste without appreciable loss of yield or reactivity. This protocol provides an alternative route for the guanylation of amines from those currently employed. Georg Thieme Verlag Stuttgart - New York.